Process of making pyrimidin derivatives.



UNITED STATES PATENT OFFICE.

MAX CONRAD, OF ASCHAFFENBURG, AND WALTER BEOKH, OF DARM- S'IADT,GERMANY.

PROCESS OF MAKING PYRiMlDlN DERIVATIVES.

Specification of Letters Patent.

Patented Feb. 6, 1906.

Original application filed November 3,1904, Serial No. 231,267. Dividedand this application filed October 21, 1906. 'Serial To all whom itn-trty concern.- 5

Be it known that we, MAX CONRAD, professor of chemistr and doctor ofphilosophy, residing at Ase ailenhurg, and W'AL'rEn BEGKH, doctor ofphilosophy, residing at Darmstadt, Germany, sub3ects of the Ger manEmperor, have invented certain new and useful Im roveinents inthcManufacture of Pyrimi in Derivatives, of which the following is aspecification.

This invention has for its object the production of pyrimidinderivatives having the constitution denoted by alkyl-4i1nino-2.6-diozgypyrimidins.

It consists in a process of condensing cyanacetic-acid esters with alkylderivatives of urea;such as methyl-urea, ethyl-urea, symmetricaldimethyl-urea, or the like-in the rcsence of condensing agents, such asthe alkali alcoholates, the alkali metals them selves, or their amids.

The following equation ma serve to illustrate the principal reaction wiich takes place in the above-characterized condensation:

ROOU N HX CO NX 1112+ 30 I 8H2 30+ ROH. lN l lliY JO i i Y In this enation R and X are equal or different alky groups. Y is hydrogen or analkyl group.

The essential characteristics of the recess thus indicated will be seenfrom the 0 lowing specific example:

Example: One hundred and thirteen parts of cyanacetic-acid ethyl esterare under proper refrigeration united with two hun iundred parts ofxylol in which forty-six parts of sodium are finely distributed, andseventy parts of methyl-urea are added. The

sodium for the most part gradually goes into solution. Thereupon forseveral hours longer the mixture is heated to about 100 to 120centigrade. Then the brown-yellow melt is carefully taken up with water,the xylol is removed, and the 3- 1nethyl-4-imino-2.fi-dioxypyrimidinwhich is formed is precipitated with acetic acid.

The process roceeds in an enalo one manner for the pro notion of otheralky -4-imino- 2.6-dioxyp rimidin derivatives by condensing other a kylor symmetrical dialkyl ureas with cyanacetic-acid esters in the presenceof alkali condensing agents.

Having now described our invention and in what manner the same is to heperformed, what we claim as new, and desire to secure by Letters Patent,is

1. The process of producing alk l--irnino- 2.6-dioxypyrimidins havingthe a )ove-given general formula, which )rocess consists in condensingalkyl-ureas o the above-characterized kind and eyanacetic-acid esters inthe presence of alkali condensing agents, substantielly as described.

2. The process of producing alkyl-tirnino- 2.6-dioxypyrimidins havingthe shove-given general formula which )IOCQSS consists in condensingalkyl-ureas oi the above-charac- .ter'ized kind and cyanacctic-acidethyl ester in the presence of alkali condensing agents, substantiallyas described.

3. The process of producing 3-methyl-4- irnino-Z.(i dioxypyrimidin,which process consists in condensing methyl-urea with cyanooetic-acidethyl ester in the presence of an alkali condensing agent, substantiallyas described.

MAX CONRAD: WALTER BECKH.

Witnesses WALTER Hoeslno, Enns'r MENNEL.

